Methanol → 6-cyano-3-methyl-1-(1-methylethyl)-1H-indole-4-carboxylic acid

HRID 593902

반응식

HRID 593902 반응식
[C:1]([C:3]1[CH:4]=[C:5]([C:16]([O:18]C)=[O:17])[C:6]2[C:7]([CH3:15])=[CH:8][N:9]([CH:12]([CH3:14])[CH3:13])[C:10]=2[CH:11]=1)#[N:2].CO.[OH-].[Na+]>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([C:16]([OH:18])=[O:17])[C:6]2[C:7]([CH3:15])=[CH:8][N:9]([CH:12]([CH3:14])[CH3:13])[C:10]=2[CH:11]=1)#[N:2]

참가 물질

5

반응물 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67467281methyl 6-cyano-1-isopropyl-3-methyl-1H-indole-4-carboxylate

생성물 1

HCID 674680896-cyano-3-methyl-1-(1-methylethyl)-1H-indole-4-carboxylic acid수율 64.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a 50 ml round bottom was added methyl 6-cyano-3-methyl-1-(1-methylethyl)-1H-indole-4-carboxylate (230 mg, 0.897 mmol), followed by methanol (1 mL) and THF (1 mL). To the solution was added 3M NaOH (0.449 mL, 2.69 mmol). The reaction stirred at rt for 20 h. The reaction was evaporated and treated with acidic water to pH 5. A brown solid crashed out and was collected by filtration. The solid was an impurity. The pH of the liquid was adjusted to 3 and the liquid was evaporated leaving a residue. Trituration of the residue with water, followed by filtration yielded 6-cyano-3-methyl-1-(1-methylethyl)-1H-indole-4-carboxylic acid (155 mg, 0.576 mmol, 64.2% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.16 (br. s., 1H) 8.33 (s, 1H) 7.78 (s, 1H) 7.66 (s, 1H) 4.81-4.98 (m, 1H) 2.33 (s, 4H) 1.45 (d, J=6.57 Hz, 6H). MS(ES) [M+H]+ 243.3.

후처리

  1. customThe reaction was evaporated
  2. additiontreated with acidic water to pH 5
  3. filtrationwas collected by filtration
  4. customthe liquid was evaporated
  5. customleaving a residue
  6. filtrationTrituration of the residue with water, followed by filtration

출처 및 근거

ORD 기록
ord-f93c731a88cc4e44b9190ace3bfd09f6
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242962B2

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